53187-38-5

Basic information

• Product Name: 1H-Pyrazole, 1-(4-methoxyphenyl)-3,5-diphenyl-
• CAS NO: 53187-38-5
• Molecular Formula: C22H18N2O
• Molecular Weight: 326.398
• Mol File: 53187-38-5.mol

Chemical Properties

• CAS DataBase Reference: 1H-Pyrazole, 1-(4-methoxyphenyl)-3,5-diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazole, 1-(4-methoxyphenyl)-3,5-diphenyl-(53187-38-5)
• EPA Substance Registry System: 1H-Pyrazole, 1-(4-methoxyphenyl)-3,5-diphenyl-(53187-38-5)

Safety Data

• Hazardous Substances Data: 53187-38-5(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 3471-32-7 4-Methoxyphenylhydrazine 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 13393-42-5 1-(4-methoxyphenyl)-3,5-diphenyl-4,5-dihydro-1H-pyrazole 
• 120-46-7 1,3-diphenylpropanedione 
• 1145-01-3 3,5-Diphenylpyrazole 
• 1448602-26-3 (4-fluorophenyl)(4-methoxyphenyl)iodonium p-toluenesulfonate 
• 27126-77-8 (4-methoxyphenyl)phenyliodonium p-toluenesulfonate 
• 69045-79-0 2-choro-5-iodopyridine 
• 100-66-3 methoxybenzene 
• 591-50-4 iodobenzene 
• 16308-14-8 4-methoxy(diacetoxyiodo)benzene 
• 696-62-8 para-iodoanisole 

Downstream Products

• 1145-01-3 3,5-Diphenylpyrazole 
• 106-51-4 p-benzoquinone 

Relevant articles and documents

TBHP/Cu(OAc)2 mediated oxidation of pyrazolines: A convenient method for the preparation of pyrazoles

An efficient and simple oxidative protocol has been developed for the preparation of pyrazoles from pyrazolines mediated by TBHP/Cu(OAc)2 at room temperature. The present protocol has been successfully applied for the preparation of various pyrazole compounds from heterocyclic pyrazolines.

Visible light mediated metal-free oxidative aromatization of 1,3,5-trisubstituted pyrazolines

The visible light mediated oxidation of 1,3,5-trisubstituted pyrazolines under metal-free conditions was developed. Various substituted pyrazolines were oxidized to pyrazoles by irradiation with visible light/sunlight. A plausible mechanism was proposed f

Biomimetic Cleavage of Aryl–Nitrogen Bonds in N-Arylazoles Catalyzed by Metalloporphyrins

The cleavage of C–N single bonds of N-containing compounds provides either an excellent nitrogen source or an excellent carbon source. In this study, an efficient metalloporphyrins/H2O2 cleavage of C–N bonds of arylpyrazoles was investigated. The effects of different factors, including different catalysts, catalyst dosages, H2O2 dosages, reaction temperature and reaction time were studied. The experimental results showed that the optimal catalyst was FeTPPCl, and the yield of pyrazole derivatives could reach up to 12.3%, which was fourfold higher than hemin catalyzed reaction and closed to ceric ammonium nitrate catalyzed reaction, respectively. Compared with transition-metal-catalyzed and strong-oxidization cleavage of C–N bonds, this protocol is characterized by environmentally-friendly, stable, mild reaction conditions and simplified operation procedures. Graphical Abstract: [Figure not available: see fulltext.].

Radical Addition of Hydrazones by α-Bromo Ketones to Prepare 1,3,5-Trisubstituted Pyrazoles via Visible Light Catalysis

A novel efficient tandem reaction of hydrazones and α-bromo ketones is reported for the preparation of 1,3,5-trisubstituted pyrazoles by visible light catalysis. In this system, the monosubstituted hydrazones show wonderful reaction activity with alkyl radicals, generated from α-bromo ketones. A radical addition followed by intramolecular cyclization affords the important pyrazole skeleton in good to excellent yields. This efficient strategy under mild conditions with wide group tolerance provides a potential approach to the 1,3,5-trisubstituted pyrazoles.

AIEE phenomenon: Tetraaryl vs. triaryl pyrazoles

Tetraarylpyrazoles are synthesized from commercially available materials in three steps and found to exhibit Aggregation Induced Emission Enhancement (AIEE) characteristics. Removing one aryl unit from tetraarylpyrazole leads to Aggregation Caused Quenching (ACQ), thus the number of aryl groups plays an important role in exploring such a phenomenon.

Transition-Metal-Free N-Arylation of Pyrazoles with Diaryliodonium Salts

A new synthetic method was developed for the N-arylation of pyrazoles using diaryliodonium salts. The transformation does not require any transition-metal catalyst and provides the desired N-arylpyrazoles rapidly under mild reaction condition in the presence of aqueous ammonia solution as a mild base without the use of inert atmosphere. The chemoselectivity of unsymmetric diaryliodonium salts was also explored with large number of examples.

Facile one-pot synthesis of 1,3,5-trisubstituted pyrazoles from α,β-enones

A practical and efficient one-pot synthesis of 1,3,5-trisubstituted pyrazoles from α,β-enones and arylhydrazine hydrochlorides has been developed. The pyrazoles were formed via a tandem formation of the corresponding pyrazolines and an acid-catalyzed aerobic oxidation process.

Copper triflate-mediated synthesis of 1,3,5-triarylpyrazoles in [bmim][PF6] ionic liquid and evaluation of their anticancer activities

A simple, efficient, and environment friendly protocol for the synthesis of 1,3,5-triarylpyrazoles and 1,3,5-triarylpyrazolines in [bmim][PF6] ionic liquid mediated by Cu(OTf)2 is described. The reaction protocol gave 1,3,5-triarylpyrazoles in good to high yields (71-84%) via a one-pot addition-cyclocondensation between chalcones and arylhydrazines, and oxidative aromatization without the requirement for an additional oxidizing reagent. The catalyst can be reused for up to four cycles without much loss in the catalytic activity. The pyrazoles (4a-o) and pyrazolines (3a-n) were evaluated for their antiproliferative activity in SK-OV-3, HT-29, and HeLa human cancer cells lines. Among all the compounds, 3b inhibited cell proliferation of HeLa cells by 80% at a concentration of 50 μM. The Royal Society of Chemistry 2013.

Copper-catalyzed aerobic C(sp2)-H functionalization for C-N bond formation: Synthesis of pyrazoles and indazoles

A simple, practical, and highly efficient synthesis of pyrazoles and indazoles via copper-catalyzed direct aerobic oxidative C(sp2)-H amination has been reported herein. This process tolerated a variety of functional groups under mild conditions. Further diversification of pyrazoles was also investigated, which provided its potential for drug discovery.

Facile access to 3,5-dihalogenated pyrazoles by sydnone cycloaddition and their versatile functionalization by Pd-catalyzed cross-coupling processes

The 1,3-dipolar cycloaddition of diversely N-substituted 4-iodosydnones with 3-halopropiolates produces easily separable mixtures of dihalogenated pyrazolylcarboxylic esters at a preparative scale level, with the 3,5-dihalogenopyrazole regioisomers always predominating. Further decarboxylation of the major isomers provided the corresponding 3,5-dihalogenopyrazoles with a free C-4 position. These were found to be valuable scaffolds for the elaboration of unsymmetrically 1,3,5-trisubstituted pyrazole derivatives by site-selective Pd-catalyzed cross-coupling reactions. Notably, the flexible and site-selective introduction of different (hetero)aryl, vinyl, or alkyl substituents at the C-5 and C-3 positions of the pyrazole core could be achieved through sequential Suzuki-type reactions with various boron compounds. Copyright